JP2001049198A - Adhesive for optical disk - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject adhesive having excellent hardenable properties at the deep position and hardly causing viscosity at the end face of light irradiation by including two kinds of photopolymerization initiators having different molar absorption coefficients. SOLUTION: The objective adhesive is obtained by including (A) 0.001-1 wt.%, preferably 0.01-0.5 wt.% photopolymerization initiator having a point having >=50 (l/mol.cm) molar absorption coefficient in 400-450 nm (e.g. 2,4,6- trimethylbenzoyldiphenylphosphine oxide), (B) 0.1-20 wt.%, preferably 0.5-10 wt.% photopolymerization initiator having <=1 (l/mol.cm) molar absorption coefficient in 400-450 nm, e.g. 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2- methyl-1-propan-1-one}, optionally (C) a radical-polymerizable oligomer, (D) a reactive diluent, and (E) an additive or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an adhesive for an optical disc and a method for manufacturing an information recording carrier using the same, and more particularly, to a method for manufacturing an information recording medium regardless of the transparency of an information recording layer or the method for manufacturing an information recording carrier. The present invention relates to an adhesive for an optical disk capable of efficiently bonding the above disks in a short time and a method for manufacturing an information recording carrier using the same.

[0002]

2. Description of the Related Art DVD
The information recording carrier represented by is usually manufactured by bonding two disks having an information recording layer on at least one side using an adhesive. When one of the two disks is light-transmitting, a radical polymerizable photocurable resin composition is usually used as an adhesive, and the radical polymerizable photocurable resin composition is applied to the two disks. A method has been adopted in which the composition is cured by irradiating light in the direction perpendicular to the disk plane from the side of the optically transparent disk and then from the light-transmitting disk side.

[0003] On the other hand, if the two disks are not light-transmitting, or if the light-transmitting is extremely small,
Usually, a slow-hardening photocurable composition which is polymerized by a hot melt adhesive or a cationic polymerization initiator is used as the adhesive.

However, when such a hot-melt adhesive is used, thermal deformation of the substrate and distortion caused by a difference in the coefficient of thermal expansion between the substrate and the adhesive due to the process of heating, cooling, and solidifying. However, there is a problem in that an information recording carrier of stable quality can be manufactured with high production efficiency. Also, when the bonded disc is heated to near the melting temperature of the hot melt adhesive, the adhesive melts out,
It has a serious problem of impairing the disk shape. On the other hand, even when using a slow-curing cationically polymerizable photocurable resin, the completion of the curing reaction of the slow-curing cationically polymerizable photoinitiator usually requires a time of several minutes to about 10 minutes. The productivity per unit time is several tenths when the radically polymerizable photocurable resin composition is used. In addition, if two disks are not completely fixed for several minutes to 10 minutes, it is not possible to obtain a disk having a constant quality, and a special fixing device is required.

[0005] From such a viewpoint, there is a demand for a method for efficiently producing a high-quality information recording carrier in a short time regardless of whether the two disks are optically transmissive or non-transmissive.

On the other hand, the present inventors used a radical-polymerizable photocurable resin composition having a high curing rate as an adhesive, and irradiated light to the outer peripheral edge and / or inner peripheral edge of two disks. From the department, it is found that a constant and high quality information recording carrier can be produced very advantageously industrially because it cures quickly and to a certain hardness, and a patent application was previously filed (Japanese Patent Application No. 10-281309). ).

According to such a manufacturing method, light irradiation is performed from the outer peripheral end or the inner peripheral end of the disk. Therefore, in order to quickly cure the disk, the photocurable resin composition has excellent deep curability ( Internal curability) is required. Then, it was found that when a photocurable resin composition having excellent deep curability was used, the light irradiation end face became viscous.

Accordingly, it is an object of the present invention to provide an adhesive for an optical disk which has excellent deep curability and does not cause viscosity of the light irradiation end face.

[0009]

Means for Solving the Problems The present inventors have proposed that a combination of an initiator having a large molar extinction coefficient at 400 nm to 450 nm and a small initiator is used as a photopolymerization initiator.
An adhesive for optical discs having excellent deep curability and having no viscosity at the light-irradiated end face can be obtained. If the adhesive is used, the two discs are made to be light-impermeable by the method described above. Also, the present inventors have found that a high-quality information recording carrier can be efficiently manufactured in a short time, and completed the present invention.

That is, the present invention relates to the following components (A) and (B): (A) a photopolymerization initiator having a point at which a molar extinction coefficient is 50 (l / mol cm) or more at 400 to 450 nm; B) An object of the present invention is to provide an optical disk adhesive containing a photopolymerization initiator having a molar extinction coefficient of 1 (l / mol cm) or less at 400 nm to 450 nm.

Further, the present invention provides a method of manufacturing an information recording carrier by bonding two disks having an information recording layer on at least one side, wherein the adhesive for an optical disk is sandwiched between the two disks. It is intended to provide a method for producing an information recording carrier, which is characterized by irradiating light from the outer peripheral end and / or inner peripheral end of the disc and curing and bonding, and an information recording carrier obtained by this method. .

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION The component (A) used in the adhesive for an optical disk of the present invention has a photopolymerization initiation point having a point at which the molar extinction coefficient in acetonitrile is at least 50 (l / mol cm) at 400 nm to 450 nm. Agent, preferably having a point at which the molar extinction coefficient is 100 (l / mol cm) or more at the wavelength. The component (A) absorbs light in the ultraviolet region. Examples of the component (A) having such properties include bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide,
Examples thereof include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, thioxanthone, diethylthioxanthone, 2-isopropylthioxanthone, and 2-chlorothioxanthone. As a commercial product, IRGA
CURE 819 (all manufactured by Ciba Specialty Chemicals Co., Ltd.), Lucirin TPO, LR8893
(Above, manufactured by BASF), KAYACURE ITX,
DETX (both manufactured by Nippon Kayaku Co., Ltd.) and the like.
Of these, 2,4,6-trimethylbenzoyldiphenylphosphine oxide is particularly preferred.

On the other hand, the component (B) is 400 nm to 450 nm.
The molar extinction coefficient in acetonitrile was 1 (l / l
mol cm) or less, and preferably has a molar extinction coefficient of 0.5 (l / mol cm) or less at the wavelength. The component (B) absorbs light in the ultraviolet region. Examples of the component (B) having such properties include 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-propan-1-one, 1-hydroxy-cyclohexyl-
Phenyl-ketone, 2,2-dimethoxy-1,2-diphenylethan-1-one, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, oligo [2-hydroxy-2-methyl-1 -[4- (1-methylvinyl) phenyl] propanone] and the like. Commercial products include IRGACURE 2959, 184, 65
1. DAROCURE 1173 (above, manufactured by Ciba Specialty Chemicals Co., Ltd.), ESACURE KIP
-100F, KIP150 (all manufactured by LAMBERTI) and the like. Among them, 1- [4- (2-hydroxyethoxy) phenyl] -2-hydroxy-2-methyl-1-propan-1-one is particularly preferred.

The component (A) is preferably incorporated in the adhesive for an optical disk of the present invention in an amount of 0.001 to 1% by weight, particularly preferably 0.01 to 0.5% by weight, from the viewpoint of deep curability. Also,
Component (B) is contained in the adhesive for a disk of the present invention in an amount of 0.1 to 2%.
0% by weight, especially 0.5 to 10% by weight, is preferable from the viewpoint of preventing the viscosity of the light irradiation end.

Thus, in the present invention, the component (A)
And the component (B) are used in combination.
It is possible to obtain the deep curability of the photocurable resin composition and the effect of preventing the end face from being irradiated with light. It is considered that component (A) among these components particularly contributes to the deep curing property, and component (B) contributes to the effect of preventing the light irradiation end face from viscous.

The components other than the above components (A) and (B) in the adhesive for an optical disk of the present invention do not impair the effects of the present invention, and are not particularly limited as long as they are incorporated into the radically polymerizable photocurable resin composition. Non-limiting examples include radically polymerizable oligomers, reactive diluents and additives.

Here, examples of the radical polymerizable oligomer include urethane (meth) acrylates (C) and the like. Urethane (meth) acrylate (C) is a polyol compound, a polyisocyanate compound and a hydroxyl group-containing (meth) acrylate compound. Is obtained by reacting

Examples of the polyol compound used include polyether polyols, polyester polyols, polycarbonate polyols, polycaprolactone polyols, aliphatic hydrocarbons having two or more hydroxyl groups in the molecule, and oils having two or more hydroxyl groups in the molecule. A cyclic hydrocarbon, an unsaturated hydrocarbon having two or more hydroxyl groups in a molecule, and the like are used. These polyols can be used alone or in combination of two or more.

Examples of the above polyether polyols include aliphatic polyether polyols, alicyclic polyether polyols, and aromatic polyether polyols.

Here, examples of the aliphatic polyether polyol include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyhexamethylene glycol, polyheptamethylene glycol, polydecamethylene glycol, pentaerythritol, dipentaerythritol, and trimethylol. Propane, triethylolpropane ethylene oxide added triol, trimethylolpropane propylene oxide added triol, trimethylolpropane ethylene oxide and propylene oxide added triol, pentaerythritol ethylene oxide added tetraol, dipentaerythritol ethylene oxide added hexa Polyvalent such as alkylene oxide-added polyols such as all Alcohol, or two or more kinds of polyether polyol obtained by ring-opening polymerization of ion-polymerizable cyclic compounds, and the like.

The alicyclic polyether polyols include
Examples thereof include alkylene oxide-added diols of hydrogenated bisphenol A, alkylene oxide-added diols of hydrogenated bisphenol F, and alkylene oxide-added diols of 1,4-cyclohexanediol.

As the aromatic polyether polyol,
For example, alkylene oxide addition diols of bisphenol A, alkylene oxide addition diols of bisphenol F, alkylene oxide addition diols of hydroquinone, alkylene oxide addition diols of naphthohydroquinone, and alkylene oxide addition diols of anthrahydroquinone are exemplified.

Commercially available polyether polyols include, for example, aliphatic polyether polyols:
PTMG650, PTMG1000, PTMG2000
(Mitsubishi Chemical Corporation), PPG1000, EXC
ENOL1020, EXENOL2020, EXCE
NOL3020, EXCENOL4020 (all manufactured by Asahi Glass Co., Ltd.), PEG1000, Unisafe DC110
0, Unisafe DC1800, Unisafe DCB110
0, Unisafe DCB1800 (above, NOF Corporation)
Manufactured), PPTG1000, PPTG2000, PPTG
4000, PTG400, PTG650, PTG200
0, PTG3000, PTGL1000, PTGL20
00 (both manufactured by Hodogaya Chemical Industry Co., Ltd.), Z-3001
-4, Z-3001-5, PBG2000, PBG20
00B (above, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), TMP30,
PNT4 glycol, EDA P4, EDA P8
(Above, manufactured by Nippon Emulsifier Co., Ltd.) and Quadrol (produced by Asahi Denka Co., Ltd.). As the aromatic polyether polyol, Uniol DA400, DA700, DA1
000, DB400 (all manufactured by NOF Corporation) and the like.

The polyester polyol is obtained by reacting a polyhydric alcohol with a polybasic acid. Here, as the polyhydric alcohol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, tetramethylene glycol, polytetramethylene glycol, 1,4-butanediol,
1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, neopentyl glycol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol,
1,2-bis (hydroxyethyl) cyclohexane,
2,2-diethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 1,9-nonanediol, 2-methyl-1,8-octanediol, glycerin, trimethylolpropane, trimethylol Examples thereof include an ethylene oxide adduct of propane, a propylene oxide adduct of trimethylolpropane, an adduct of ethylene oxide and propylene oxide of trimethylolpropane, sorbitol, pentaerythritol, dipentaerythritol, and an alkylene oxide-added polyol. Examples of the polybasic acid include phthalic acid, isophthalic acid, terephthalic acid, maleic acid, fumaric acid, adipic acid, sebacic acid and the like. Commercial products of these polyester polyols include Clapol P1010, Clapol P2010, PMIPA, P
KA-A, PKA-A2, PNA-2000 (or more,
(Kuraray Co., Ltd.) can be used.

The polycarbonate polyol includes, for example, a polycarbonate diol represented by the formula (1).

[0026]

Embedded image

Wherein R ¹ represents an alkylene group having 2 to 20 carbon atoms, a (poly) ethylene glycol residue, a (poly) propylene glycol residue, or a (poly) tetramethylene glycol residue; It is an integer of 30.)

Specific examples of R ¹ include residues obtained by removing hydroxyl groups at both terminals from the following compounds, ie, 1,4-butanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, 1,7-heptanediol, 1,8
-Octanediol, 1,9-nonanediol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, and the like, from which a hydroxyl group is removed. Commercially available polycarbonate polyols include DN-980 and DN-98.
1, DN-982, DN-983 (all manufactured by Nippon Polyurethane Industry Co., Ltd.), PC-8000 (manufactured by PPG),
PNOC1000, PNOC2000, PMC100,
PMC2000 (all made by Kuraray Co., Ltd.), Praxel CD-205, CD-208, CD-210, CD-
220, CD-205PL, CD-208PL, CD-
210PL, CD-220PL, CD-205HL, C
D-208HL, CD-210HL, CD-220H
L, CD-210T, CD-221T (all manufactured by Daicel Chemical Industries, Ltd.) and the like can be used.

As the polycaprolactone polyol, ε-caprolactone is used, for example, ethylene glycol, polyethylene glycol, propylene glycol,
Addition to diols such as polypropylene glycol, tetramethylene glycol, polytetramethylene glycol, 1,2-polybutylene glycol, 1,6-hexanediol, neopentyl glycol, 1,4-cyclohexanedimethanol, 1,4-butanediol And polycaprolactone diol obtained by the reaction. These commercial products include Plaxel 205, 2
05AL, 212, 212AL, 220, 220AL
(Above, manufactured by Daicel Chemical Industries, Ltd.) and the like can be used.

Examples of the aliphatic hydrocarbon having two or more hydroxyl groups in the molecule include ethylene glycol, propylene glycol, tetramethylene glycol, 1,4-butanediol, 1,5-pentanediol, and 1,6-hexanediol. 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, neopentyl glycol, 2,2-diethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2-methyl-1,8-octanediol, hydroxy-terminated hydrogenated polybutadiene, glycerin, trimethylolpropane, pentaerythritol, sorbitol and the like.

Examples of the alicyclic hydrocarbon having two or more hydroxyl groups in the molecule include 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, and 1,2-cyclohexanediol.
Examples include bis (hydroxyethyl) cyclohexane, a dimethylol compound of dicyclopentadiene, and tricyclodecanedimethanol.

Examples of the unsaturated hydrocarbon having two or more hydroxyl groups in the molecule include hydroxy-terminated polybutadiene and hydroxy-terminated polyisoprene.

Further, other polyols other than the above include, for example, β-methyl-δ-valerolactone diol,
Castor oil-modified diols, terminal diol compounds of polydimethylsiloxane, polydimethylsiloxane carbitol-modified diols, and the like.

The number average molecular weight of these polyol compounds is preferably from 50 to 15,000, more preferably from 100 to 15,000.
8000.

The polyisocyanate compound is preferably a diisocyanate compound.
-Tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,3-xylylene diisocyanate,
1,4-xylylene diisocyanate, 1,5-naphthalene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 3,3′-dimethyl-4,4′-diphenylmethane diisocyanate,
4,4'-diphenylmethane diisocyanate, 3,3
'-Dimethylphenylene diisocyanate, 4,4'-
Biphenylene diisocyanate, 1,6-hexane diisocyanate, isophorone diisocyanate, 2,2
4-trimethylhexamethylene diisocyanate, bis (2-isocyanateethyl) fumarate, 6-isopropyl-1,3-phenyl diisocyanate, 4-diphenylpropane diisocyanate, lysine diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, tetramethyl xylylene And diisocyanates. Of these, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hydrogenated xylylene diisocyanate,
Isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate and the like are preferred. These diisocyanates can be used alone or in combination of two or more.

The hydroxyl group-containing (meth) acrylate is a (meth) acrylate having a hydroxyl group in an ester residue.
For example, 2-hydroxyethyl (meth) acrylate, 2
-Hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxy-
3-phenyloxypropyl (meth) acrylate,
1,4-butanediol mono (meth) acrylate, 2
-Hydroxyalkyl (meth) acryloyl phosphate, 4-hydroxycyclohexyl (meth) acrylate, 1,6-hexanediol mono (meth) acrylate, neopentyl glycol mono (meth) acrylate, trimethylolpropane di (meth) acrylate,
Trimethylolethanedi (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, or (meth) acrylate represented by the following structural formula (2), and the like.

[0037]

Embedded image

Wherein R ² represents a hydrogen atom or a methyl group, and n represents an integer of 1 to 15, preferably 1 to 4.
Further, compounds obtained by an addition reaction of a glycidyl group-containing compound such as alkyl glycidyl ether, allyl glycidyl ether, glycidyl (meth) acrylate and (meth) acrylic acid can also be mentioned. Of these, 2-hydroxyethyl (meth) acrylate,
Hydroxyalkyl (meth) acrylates such as 2-hydroxypropyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate are preferred.

The method for synthesizing the urethane (meth) acrylate is not particularly limited. For example, the method is performed according to the following methods (i) to (iii). (I) A method of reacting (b) a polyisocyanate and (c) a hydroxyl group-containing (meth) acrylate, followed by (a) a polyol. (Ii) (a) a polyol, (b) a polyisocyanate,
(C) A method in which a hydroxyl group-containing (meth) acrylate is charged at once and reacted. (Iii) A method in which (a) a polyol and (b) a polyisocyanate are reacted, and then (c) a hydroxyl group-containing (meth) acrylate is reacted.

In the synthesis of urethane (meth) acrylate, copper naphthenate, cobalt naphthenate, zinc naphthenate, di-n-butyltin dilaurate, triethylamine, 1,4-diazabicyclo [2.2.2] octane, 1,4-diaza-2-methylbicyclo [2.
2.2] The reaction is preferably carried out using a urethanization catalyst such as octane in an amount of 0.01 to 1 part by weight based on 100 parts by weight of the total amount of the reactants. The reaction temperature in this reaction is usually 0 to 90 ° C, preferably 10 to 80 ° C.

The preferred number average molecular weight of the urethane (meth) acrylate is from 400 to 40,000, especially 60.
It is preferably from 0 to 20,000.

These urethane (meth) acrylates (C) are preferably incorporated in the adhesive for optical disks of the present invention in an amount of 5 to 90% by weight, particularly 10 to 80% by weight.

Examples of the reactive diluent that can be used in the present invention include (meth) acrylate compounds having at least one (meth) acryloyl group in one molecule. As these components, any of a monofunctional compound having only one (meth) acryloyl group and a polyfunctional compound having two or more (meth) acryloyl groups may be used, and may be used together in an appropriate ratio.

As the monofunctional compound, (D) hydroxyalkyl (meth) acrylate such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, etc. It is preferably used from the viewpoint of improving moist heat resistance. Also, as other monofunctional compounds,
For example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, amyl (meth) acrylate, isobutyl (meth)
Acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, isoamyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl ( Meth) acrylate, nonyl (meth) acrylate,
Decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, octadecyl (meth) acrylate, stearyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, Butoxyethyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenoxyethyl (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, methoxy Ethylene glycol mono (meth) acrylate, ethoxyethyl (meth) acrylate, ethoxyethoxyethyl (meth Acrylate, methoxy polyethylene glycol (meth) acrylate, methoxy polypropylene glycol (meth) acrylate, dicyclopentadienyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, tricyclodecanyl ( (Meth) acrylate, bornyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 7-
Amino-3,7-dimethyloctyl (meth) acrylate, (meth) acryloylmorpholine, 2- (meth) acryloyloxyethyl phthalic acid, 2- (meth) acryloyloxyethyl hexahydrophthalic acid, 2- (meth) acryloyloxy Propylphthalic acid, 2- (meth) acryloyloxypropyltetrahydrophthalic acid, 2- (meth) acryloyloxypropylhexahydrophthalic acid, 2- (meth) acryloyloxyethylsuccinic acid, trifluoroethyl (meth) acrylate,
Tetrafluoropropyl (meth) acrylate, hexafluoropropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, mono [2- (meth) acryloyloxyethyl] phosphate, mono [2- (Meth) acryloyloxyethyl] diphenyl phosphate, mono [2- (meth) acryloyloxypropyl]
Phosphates and compounds represented by the following formulas (3) to (5) can be exemplified.

[0045]

Embedded image

[Wherein, R ³ represents an alkylene group or a hydroxyalkylene group having 2 to 6 carbon atoms, R ⁴ represents a hydrogen atom or a methyl group, and R ⁵ represents a hydrogen atom or a 1 to 1 carbon atom.
12 represents an alkyl group, and p represents an integer of 0 to 20. ]

[0047]

Embedded image

Wherein R ⁶ represents a hydrogen atom or a methyl group, R ⁷ represents an alkylene group having 2 to 8 carbon atoms, and q represents 0
Shows an integer of ~ 8. ]

[0049]

Embedded image

Wherein R ⁸ represents a hydrogen atom or a methyl group, R ⁹ represents an alkylene group having 2 to 8 carbon atoms, and r represents 0
And R ¹⁰ and R ¹¹ are a hydrogen atom and a carbon number of 1
And 6 to 6 alkyl groups. ]

[0051] These commercial products include Aronix.
M101, M102, M110, M111, M113,
M114, M117, M120, M152, M154,
M5300, M5400, M5500, M5600 (all manufactured by Toagosei Co., Ltd.), KAYARAD TC-11
OS, R-128H, R629, R644 (all manufactured by Nippon Kayaku Co., Ltd.), IPAA, AIB, SBAA, TB
A, IAAA, HEXA, CHA, NOAA, IOA
A, INAA, LA, TDA, MSAA, CAA, HD
AA, LTA, STA, ISAA-1, ODAA, ND
AA, IBXA, ADAA, TCDA, 2-MTA, D
MA, VISCOAT # 150, # 150D, # 155,
# 158, # 160, # 190, # 190D, # 19
2, # 193, # 220, # 320, # 2311HP,
# 2000, # 2100, # 2150, # 2180, M
TG (all manufactured by Osaka Organic Chemical Industry Co., Ltd.), NK ester M-20G, M-40G, M-90G, M-230
G, CB-1, SA, S, AMP-10G, AMP-2
0G, AMP-60G, AMP-90G, A-SA, N
LA (all manufactured by Shin-Nakamura Chemical Co., Ltd.), ACMO
(Made by Kojin Co., Ltd.), Light Acrylate IA-A, L
-A, SA, BO-A, EC-A, MTG-A, DP
MA, PO-A, P-200A, THF-A, IB-
XA, HOA-MS, HOA-MPL, HOA-MP
E, HOA-HH, IO-A, BZ-A, NP-EA,
NP-10EA, HOB-A, FA-108, epoxy ester M-600A, light ester PM (or more,
Kyoeisha Chemical Co., Ltd.), FA-511, FA-512
A, FA-513A (manufactured by Hitachi Chemical Co., Ltd.),
AR-100, MR-100, MR-200, MR-2
60 (manufactured by Daihachi Chemical Co., Ltd.), JAMP-100,
JAMP-514 and JPA-514 (all manufactured by Johoku Chemical Co., Ltd.) and the like.

Examples of the polyfunctional compound include ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexanediol di (meth) acrylate. ) Acrylate, 1,9-nonanediol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth)
Acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate hydroxypivalate, tri Methylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate , Trimethylolpropane trioxyethyl (meth) acrylate, trimethylolpropane polyoxyethyl (meth) Acrylate, trimethylolpropane tri propyl (meth) acrylate, trimethylolpropane polyoxyethylene (meth)
Acrylate, tris (2-hydroxyethyl) isocyanurate di (meth) acrylate, tris (2-hydroxyethyl) isocyanurate tri (meth) acrylate, ethylene oxide-added bisphenol A di (meth) acrylate, ethylene oxide-added bisphenol F di (meth) Acrylate, propylene oxide added bisphenol A di (meth) acrylate, propylene oxide added bisphenol F di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, bisphenol A diepoxy di (meth) acrylate, bisphenol F diepoxy di (meth) acrylate , Bis [2- (meth) acryloyloxyethyl]
Examples include (E) polyfunctional (meth) acrylates such as phosphate, bis [2- (meth) acryloyloxypropyl] phosphate, and tris [2- (meth) acryloyloxyethyl] phosphate. When the monofunctional (meth) acrylate is used in combination with the component (B), the monofunctional (meth) acrylate is effective in preventing the viscosity of the light irradiation end.

These commercial products include SA-100
2, SA-2006, SA-2007, SA-410
0, SA-5001, SA-6000, SA-760
0, SA-8000, SA-9000 (all manufactured by Mitsubishi Chemical Corporation), VISCOAT # 195, # 195D, # 2
14HP, # 215, # 215D, # 230, # 230
D, # 260, # 295, # 295D, # 300, # 3
10HP, # 310HG, # 312, # 335HP, #
335D, # 360, GPT, # 400, V # 540,
# 700, GPT (above, Osaka Organic Chemical Industry Co., Ltd.)
KAYARALMANDA, R-526, NPG
DA, PEG400DA, R-167, HX-220,
HX-620, R-551, R-712, R-604,
R-684, GPO-303, TMPTA, THE-3
30, TPA-320, TPA-330, PET-3
0, RP-1040, T-1420, DPHA, D-3
10, D-330, DPCA-20, DPCA-30,
DPCA-60, DPCA-120 (all manufactured by Nippon Kayaku Co., Ltd.), Aronix M-210, M-208,
M-215, M-220, M-225, M-233, M
-240, M-245, M-260, M-270, M-
305, M-309, M-310, M-315, M-3
20, M-350, M-360, M-400, M-40
8, M-450 (all manufactured by Toagosei Co., Ltd.), SR-2
12, SR-213, SR-355 (all manufactured by Sartomer), SP-1506, SP-1507, SP-15
09, SP-1519-1, SP-1563, SP-2
500, VR60, VR77, VR90 (all, manufactured by Showa Polymer Co., Ltd.), Light Ester P-2M (all, manufactured by Kyoeisha Chemical Co., Ltd.), Biscoat 3PA (manufactured by Osaka Organic Chemical Industry Co., Ltd.), EB- 169, EB-179, EB-3
603, R-DX63182 (Daicel UCB
And the like).

As the reactive diluent, a radical polymerizable compound other than the compound containing a (meth) acryl group can be included. Examples of such a compound include N-vinylpyrrolidone, N-vinylcaprolactam, vinyl acetate, vinyl propionate, styrene, divinylbenzene, and unsaturated polyester. The unsaturated polyester is an ester of a dicarboxylic acid having a radical polymerizable unsaturated double bond and an alcohol, and examples of the dicarboxylic acid having a radical polymerizable unsaturated double bond include maleic anhydride, itaconic acid, and fumaric acid. And alcohols such as methanol, ethanol,
n-propyl alcohol, iso-propyl alcohol, n-butyl alcohol, iso-butyl alcohol, sec-butyl alcohol, tert-butyl alcohol, n-hexanol, cyclohexanol, 2-
Monohydric alcohols such as ethylhexyl alcohol; (poly) ethylene glycols such as ethylene glycol, diethylene glycol and triethylene glycol; (poly) propylene glycols such as propylene glycol, dipropylene glycol and tripropylene glycol;
Dihydric alcohols such as 1,6-hexanediol; and trihydric alcohols such as glycerin and trimethylolpropane.

Of these reactive diluents, it is particularly preferable to use a combination of (D) hydroxyalkyl (meth) acrylate and (E) polyfunctional (meth) acrylate.

The reactive diluent is preferably incorporated in the adhesive for an optical disk of the present invention in an amount of 10 to 95% by weight, particularly preferably 20 to 90% by weight. Among them, the component (D) is 10 to 9
It is preferable to add 5% by weight, especially 20 to 90% by weight. Component (E) is 0.1 to 50% by weight, particularly 0.5% by weight.
It is preferable to mix 〜40% by weight.

The additives include epoxy resin, polyamide, polyamideimide, polyurethane, polybutadiene, chloroprene, polyether, polyester,
Pentadiene derivative, SBS (styrene / butadiene /
Styrene block copolymer), hydrogenated SBS, SIS
(Styrene / isoprene / styrene block copolymer), petroleum resin, xylene resin, ketone resin, fluorine-based oligomer, silicone-based oligomer, polysulfide-based oligomer, and the like.

Furthermore, various paint additives other than those described above, for example, antioxidants, ultraviolet absorbers, light stabilizers, antioxidants, silane coupling agents, defoamers, leveling agents, antistatic agents, surfactants, and preservatives Stabilizer, thermal polymerization inhibitor, plasticizer,
A wettability improver and the like can be blended as needed.
For example, antioxidants include Irganox 24
5, 259, 565, 1010, 1035, 1076,
1081, 1098, 1222, and 1330 (all manufactured by Ciba Specialty Chemicals Co., Ltd.).

Examples of the ultraviolet absorber include benzotriazole-based and triazine-based ultraviolet absorbers, and commercially available products include Tinuvin P, 234, 320 and 32.
6, 327, 328, 213, 400 (all manufactured by Ciba Specialty Chemicals Co., Ltd.), Sumisorb
110, 130, 140, 220, 250, 300, 3
20, 340, 350, and 400 (all manufactured by Sumitomo Chemical Co., Ltd.).

As the light stabilizer, Tinuvin 14
4,292,622LD (all manufactured by Ciba Specialty Chemicals Co., Ltd.) SANOL LS440, LS770
(The above are manufactured by Sankyo Co., Ltd.), Sumisorb TM-0
61 (manufactured by Sumitomo Chemical Co., Ltd.).

Examples of the antioxidants include phenolic antioxidants, allylamine antioxidants, ketoneamine antioxidants, and the like.
ene W, S, P, 3C, 6C, RD-G, FR,
AW (above, manufactured by Sumitomo Chemical Co., Ltd.) and the like.
Examples of the silane coupling agent include γ-mercaptopropylmethylmonomethoxysilane, γ-mercaptopropylmethyldimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-mercaptopropylmonoethoxysilane, γ-mercaptopropyldiethoxysilane, γ
-Mercaptopropyltriethoxysilane, β-mercaptoethylmonoethoxysilane, β-mercaptoethyltriethoxysilane, β-mercaptoethyltriethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-glycidoxylpropyltrimethoxysilane, γ-glycidoxylpropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ) Ethyltrimethoxysilane, γ-chloropropylmethyldimethoxysilane, γ-chloropropyltrimethoxysilane, γ-methacryloyloxypropyltrimethoxysilane and the like. These commercially available products include Silaace S310, S311 and S3
20, S321, S330, S510, S520, S5
30, S610, S620, S710, S810 (all manufactured by Chisso Corporation), SH6062, AY43-06
2, SH6020, SZ6023, SZ6030, SH
6040, SH6076, SZ6083 (Toray,
Dow Corning Silicone Co., Ltd.), KBM40
3, KBM503, KBM602, KBM603, KB
M803, KBE903 (above, Shin-Etsu Silicone Co., Ltd.)
Manufactured).

As the defoaming agent, Floren AC-20
2, AC-300, AC-303, AC-326F, A
C-900, AC-1190, AC-2000 (or more,
Organic copolymers not containing Si or F atoms, examples of which are Floren AC-901 and AC-
950, AC-1140, AO-3, AO-4OH (all manufactured by Kyoeisha Yushi Co., Ltd.), FS1265, SH20
0, SH5500, SC5540, SC5570, F-
1. Silicon antifoaming agents such as SD5590 (all manufactured by Dow Corning Toray Silicone Co., Ltd.), Megafac F-142D, F-144D, F-178K, F-17
9, F-815 (above, Dainippon Ink and Chemicals, Inc.)
And other fluorine atom-containing defoamers.

As the leveling agent, Polyflow No.
7, no. 38, no. 50E, S, 75, No. 7
5, no. 77, No. 90, no. 95, no. 30
0, No. 460, ATF, KL-245 (all manufactured by Kyoeisha Yushi Co., Ltd.) and the like.

The adhesive for an optical disk is preferably liquid at room temperature, but from the viewpoint of applicability, it is preferably from 2 to 8,000.
0 mPa · s is preferred, and especially 10 to 6,000 mPa · s
Is preferred.

The adhesive for an optical disk of the present invention can be used in any method as long as it is a method for producing an information recording carrier in which two disks are bonded together. A method for manufacturing an information recording carrier by bonding two disks having an information recording layer on at least one side, wherein an optical disk adhesive is sandwiched between the two disks, and the outer edge of the disk is It is preferably used in a method of irradiating light from a portion and / or an inner peripheral end portion to cure and adhere (hereinafter, referred to as a method of the present invention).

The two disks used in the method of the present invention are ones having one or both of the information recording layers.
A disc having such an information recording layer is one in which unevenness corresponding to recorded information is provided on one surface of a well-known and commonly used plastic substrate, and a light reflecting film layer is laminated thereon. Alternatively, it is a writable optical information recording carrier in which a light reflecting film layer is laminated on a recording layer containing a dye on a plastic substrate. Here, examples of the plastic of the plastic substrate include thermoplastic synthetic resins such as acrylic, polycarbonate, and amorphous polyolefin resin.

The film preferably reflects the visible light employed for reading recorded information at a high rate to accurately confirm the irregularities. For example, aluminum, nickel, silver, gold, silicon nitride, silicon carbide, or the like can be used. And the like.

The disk used in the method of the present invention is obtained by casting the material to be the substrate on a stamper having a predetermined size, shape and thickness, for example, in which grooves corresponding to reproduction information such as sound and video are engraved. After that, it can be obtained by laminating a light-reflective coating thereon. In general, this lamination can be performed by depositing the metal to a predetermined thickness on the groove surface of the substrate provided with the groove to form a metal thin film (pit formation). Thus, an information recording layer in which the groove and the film are integrated is formed. In the case of a writable optical information recording carrier, instead of providing physical irregularities on the substrate, a recording layer containing an organic dye compound such as a cyanine-based or phthalocyanine-based dye is formed,
On this recording layer, a reflective layer made of a metal thin film is formed by the same method as described above.

In the method of the present invention, it is preferable that individual or continuous information is recorded on the information recording layers of two disks.

In order to sandwich the adhesive for an optical disk between two disks in the method of the present invention, the adhesive may be applied to one surface of one or both disks and the applied surfaces may be bonded together. The method of applying the adhesive is not particularly limited, and is performed by, for example, a spin coater, a roll coater, a screen printing method, or the like. The thickness of the coating film is preferably from 1 to 200 μm, particularly preferably from 10 to 100 μm.

Next, ultraviolet rays are radiated from the outer peripheral end and / or the inner peripheral end of the two discs sandwiched (see FIG. 1) to carry out hardening and bonding. Irradiation from the outer edge is preferable from the viewpoint of the size of the device, but is not limited to the shape of the device. High-pressure mercury lamps, metal halide lamps, xenon lamps, ultraviolet lasers, etc. are used as light sources,
It is particularly preferable to use a lamp having a wavelength of 320 nm to 450 nm or a laser, and a high pressure mercury lamp and a metal halide lamp are particularly preferable.

The light irradiation may be performed from one place.
It is preferable to carry out from more than two places, and it is particularly efficient to carry out from two to eight peripheral ends. Furthermore, when irradiating,
It is more preferable to rotate the disks in order to achieve uniform and efficient curing (see FIG. 1).

As a more preferable specific example of the light irradiation, 2
A method of irradiating a light beam from two or more positions on the outer peripheral end of the disk while rotating the disks is used.

As the information recording carrier obtained by the method of the present invention, high-density information typified by optical disks such as DVD (digital video (or versatile) disk), MO (magneto-optical disk), and PD (phase change optical disk) Record carriers.

[0075]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

Synthesis Example 1 In a 1-liter separable flask equipped with a stirrer and a thermometer, 209 g of isophorone diisocyanate, 3,5-
0.2 g of di-t-butyl-4-hydroxytoluene,
0.8 g of di-n-butyltin dilaurate was charged and stirred, and cooled to 10 ° C. in a cold water bath under a dry air atmosphere.
109 g of 2-hydroxyethyl acrylate was added little by little over 1 hour so that the content was maintained at 10 to 35 ° C., and the mixture was reacted. Thereafter, the hydroxyl value is 109.7 mgKOH / g.
Polytetramethylene glycol (trade name: PTMG1
480g, manufactured by Mitsubishi Chemical Corporation)
Stirring was continued at 0 ° C. for 5 hours to cause a reaction. Thereafter, the reaction product was taken out to obtain a urethane acrylate (C1) having a number average molecular weight of 1650.

Synthesis Example 2 Polyester diol having a hydroxyl value of 111.7 mgKOH / g (trade name: Kurapol P1010, manufactured by Kuraray Co., Ltd.) instead of polytetramethylene glycol of Synthesis Example 1
The same operation as in Synthesis Example 1 was carried out except that 72 g was used,
Urethane acrylate having a number average molecular weight of 1530 (C2)
I got

Examples and Comparative Examples <Preparation of Adhesive for Optical Disk> Each component having the composition shown in Table 1 was added to a reaction vessel equipped with a stirrer, followed by stirring and mixing. The adhesives of Examples 1-2 were prepared. Each component in Table 1 is as follows.

(A) Component A1: 2,4,6-trimethylbenzoyldiphenylphosphine oxide (commercially available product: Lucirin TPO,
BASF, molar absorption coefficient at 400 nm about 490
(L / mol cm) A2: bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide (commercial product: IRGACURE)
819, manufactured by Ciba Specialty Chemicals Co., Ltd., 40
Molar extinction coefficient at 0 nm about 660 (l / mol cm))

(B) Component B1: 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propane-1-
ON (commercial product: IRGACURE2959, manufactured by Ciba Specialty Chemicals Co., Ltd., molar extinction coefficient at 400 nm almost 0 (l / mol cm)) B2: 1-hydroxy-cyclohexyl-phenyl-ketone (commercial product: IRGACURE184, Ciba Specialty Chemicals ( Co., Ltd., molar extinction coefficient at 400 nm is almost 0 (l / mol cm))

(D) Component D1: 4-hydroxybutyl acrylate (commercial product: 4
-HBA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) D2: 2-hydroxyethyl acrylate (commercial product: H
EA, manufactured by Osaka Organic Chemical Industry Co., Ltd.)

(E) Component E1: Pentaerythritol tetraacrylate (commercially available product: KAYARDADDPHA, manufactured by Nippon Kayaku Co., Ltd.) E2: Trimethylolpropane triacrylate (commercially available product: Biscoat 295, manufactured by Osaka Organic Chemical Industry Co., Ltd.)

Next, using the adhesives prepared as described above (Examples 1 and 2 and Comparative Examples 1 and 2), the deep curing property and the light irradiation end face curing property of each adhesive were as follows. Was evaluated as follows. Deep curability Using two aluminum substrates sputtered on a PC substrate, using a spin coater so that the coating thickness is about 50 μm, and rotating from the side with an apparatus as shown in FIG. A high-pressure mercury lamp was used as a light source, and light of 3000 mJ / cm ² was applied to bond the two substrates. After that, when the bonded disc was peeled off,
A case where an uncured liquid portion was found inside was judged to be poor in deep-section curability, and was indicated by "X" in Table 1. In addition, when no liquid portion was observed, it was determined that the deep part curability was good, and the result was indicated by “○” in Table 1.

When the light-irradiated end face of the discs bonded together as in the light-irradiated end face curl property was touched, the case where there was tack (viscosity) was judged to be poor in the light-irradiated end face curability, and was marked X in Table 1. . In addition, when there was no tack, it was judged that the light-irradiated end face curability was good, and the result was indicated by “○” in Table 1.

Table 1 shows the results of the above evaluations of the examples and comparative examples. From these results, it can be seen that both Examples 1 and 2 are excellent in deep part curability and light irradiation end face curability. Comparative Example 1 containing no component (A) had poor deep-section curability. Comparative Example 2 containing no component (B) had poor light-irradiated end face curability.

[0086]

[Table 1]

[0087]

The adhesive for an optical disk according to the present invention is used in a method for manufacturing an information recording carrier by bonding two disks, and after sandwiching the two disks, the outer peripheral edge and / or the inner side of the disk. It can be cured by irradiating light from the peripheral edge, and the resulting bonded disc has excellent deep curability and light irradiation end face curability. It is extremely useful as compared with agents.

[Brief description of the drawings]

FIG. 1 is a schematic view of a method of irradiating ultraviolet rays from outer peripheral ends of two disks.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Takayoshi Tanabe 2--11-24 Tsukiji, Chuo-ku, Tokyo Inside JSR Corporation (72) Inventor Takashi Ukaji 2-11-24 Tsukiji, Chuo-ku, Tokyo Jay F Co., Ltd. F-term (reference) 4J011 QA03 QA04 QA08 QA09 QA12 QA13 QA17 QA18 QA19 QA22 QA23 QA24 QA25 QA32 QA33 QA34 QA37 QA38 QA39 QA42 QA45 QA46 QB12 QB13 QB16 TA02 AC02 SA04 AC04 AG03 AG04 AG05 AG06 AG09 AG12 AG23 AG24 AG27 AJ08 BA02 BA04 BA05 BA07 BA08 BA10 BA11 BA12 BA13 BA15 BA16 BA18 BA19 BA20 BA21 BA23 BA24 BA26 BA27 CA02 CA04 CA06 CA07 CA08 CA10 CB10 CC05 CD09 4J040 FA131 FA132 FA141 FA142 FA151 FA152 FA161 FA162 FA162 FA212 FA261 FA262 FA291 FA292 GA02 HB19 HD19 HD27 JB08 KA13 KA24 LA01 LA11 NA17 NA21 PA 32 5D029 RA30

Claims (7)

[Claims] 1. The following components (A) and (B), (A) 40
The molar extinction coefficient is 50 (l / mol) from 0 nm to 450 nm.
cm) or more, (B) 400
The molar extinction coefficient is 1 (l / mol cm) between nm and 450 nm.
An optical disc adhesive containing the following photopolymerization initiator. 2. The optical disk adhesive according to claim 1, wherein the content of the component (A) is 0.001 to 1% by weight and the content of the component (B) is 0.1 to 20% by weight. 3. The adhesive for optical disks according to claim 1, wherein the component (A) is 2,4,6-trimethylbenzoyldiphenylphosphine oxide. 4. The component according to claim 1, wherein the component (B) is 1- [4- (2-hydroxyethoxy) phenyl] -2-hydroxy-2-methyl-1-propan-1-one. 2. The adhesive for optical disks according to claim 1. 5. A urethane (meth) acrylate obtained by further reacting the following components (C), (D) and (E) (C) a polyol compound, a polyisocyanate compound and a hydroxyl group-containing (meth) acrylate compound; 5. It contains (D) hydroxyalkyl (meth) acrylate and (E) polyfunctional (meth) acrylate.
The adhesive for an optical disk according to any one of the above items. 6. At least one of which has an information recording layer
In a method for manufacturing an information recording carrier by bonding two disks, after sandwiching the optical disk adhesive according to any one of claims 1 to 5 between two disks, the outer peripheral edge of the disks and / or Alternatively, a method for producing an information recording carrier, comprising irradiating light from the inner peripheral end and curing and bonding. 7. An information recording carrier manufactured by the manufacturing method according to claim 6.